Synthesis and crystal structure of a new pyridinium bromide salt: 4-methyl-1-(3-phenoxypropyl)pyridinium bromide

Abstract

In the cation of the title molecular salt, C15H18NO+·Br−, the pyridinium and phenyl rings are inclined to one another by 11.80 (8)°. In the crystal, the Br− anion is linked to the cation by a C—H...Br hydrogen bond. The cations stack along the b-axis direction and are linked by further C—H...Br interactions, and offset π–π interactions [intercentroid distances = 3.5733 (19) and 3.8457 (19) Å], forming slabs parallel to the ab plane. The effects of the C—H...X− interaction on the NMR signals of the ortho- and meta-pyridinium protons in a series of related ionic liquids, viz. 4-methyl-1-(4-phenoxybutyl)pyridin-1-ium salts, are reported and discussed.

Keywords

• crystal structure
• ionic liquids
• pyridinium salts
• halide
• hydrogen bonding
• π–π interactions